Let's put Tailscale on a jailbroken Kindle
Learn how to install Tailscale on a jailbroken Kindle and use SSH, Taildrop, MagicDNS, and remote access to extend what your Kindle can do.
Mitanshu Sukhwani recently wrote a blog post detailing how to install Tailscale on a jailbroken Kindle. Jailbreaking a Kindle refers to removing the software restrictions imposed by its manufacturer, granting users root access to the device’s operating system. This allows for accessing internal system components, running unauthorized software, and increasing the device’s functionality beyond the intended use.
Kindle jailbreaking has a history, with the first jailbreak debuting months after the iPhone’s release and occurring every so often. Currently, a method called AdBreak is available for all Kindle models except the latest ones (running firmware version 5.18.5.0.2 or newer). Sukhwani uses an 11th-generation Kindle running on Tailscale, enabling him to transfer files via SSH or Taildrop, as well as run various unofficial apps like KOReader and a self-hosted Calibre Web library. These enhancements make the e-reader more versatile and open to third-party, DRM-free ebooks.
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